AU555477B2 - Alkane and alkene derivatives - Google Patents

Alkane and alkene derivatives

Info

Publication number
AU555477B2
AU555477B2 AU89702/82A AU8970282A AU555477B2 AU 555477 B2 AU555477 B2 AU 555477B2 AU 89702/82 A AU89702/82 A AU 89702/82A AU 8970282 A AU8970282 A AU 8970282A AU 555477 B2 AU555477 B2 AU 555477B2
Authority
AU
Australia
Prior art keywords
sub
compounds
hydrogen
carbon atoms
hydroxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
AU89702/82A
Other versions
AU8970282A (en
Inventor
Guillermo Luis Blanco
Lauri Veikko Matti Kangas
Arto Johannes Karjalainen
Kauko Oiva Antero Kurkela
Marja-Liisa Sodervall
Reijo Juhani Toivola
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Farmos Yhtyma Oy
Original Assignee
Farmos Yhtyma Oy
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Farmos Yhtyma Oy filed Critical Farmos Yhtyma Oy
Publication of AU8970282A publication Critical patent/AU8970282A/en
Application granted granted Critical
Publication of AU555477B2 publication Critical patent/AU555477B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
    • C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
    • C07C37/003—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by hydrogenation of an unsaturated part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/11—Alkylated hydroxy benzenes containing also acyclically bound hydroxy groups, e.g. saligenol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
    • C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Epoxy Compounds (AREA)
  • Steroid Compounds (AREA)
  • Inorganic Insulating Materials (AREA)
  • Separation Of Gases By Adsorption (AREA)
  • Treating Waste Gases (AREA)

Abstract

The invention provides novel compounds of the formulaorwherein R<sub>1</sub> is hydrogen, hydroxy, alkoxy of 1 to 4 carbon atoms, benzyloxy, allyloxy, 2,3-epoxypropoxy, 2,3-dihydroxypropoxy, methoxymethoxy, ethoxymethoxy, or wherein one of R<sub>5</sub> and R<sub>6</sub> is hydrogen or R<sub>5</sub> and R<sub>6</sub> are alkyl groups of 1-4 carbon atoms which may be the same or different, or the -NR<sub>5</sub>R<sub>6</sub> group stands for a nitrogen containing 5 to 7 membered heterocyclic radial and m is 1 or 2; R<sub>2</sub> is an alkyl of 1 to 4 carbon atomswherein R<sub>7</sub> has the same meanings as R<sub>1</sub>, except that R<sub>7</sub> and R, cannot simultaneously be the same; R<sub>3</sub> is an alkyl of 2 to 4 carbon atoms, cyclopentyl or hydroxy-cyclopentyl; R<sub>4</sub> is hydrogen or hydroxy; and n is 0 to 3, provided that when R<sub>4</sub> is hydrogen, then R<sub>2</sub> and R<sub>3</sub> are not simultaneously lower alkyl containing up to 4 carbon atoms, and their non-toxic pharmaceutically acceptable acid addition salts and esters and mixtures thereof. Processes for the preparation of these compounds are described, as are novel pharmaceutical compositions of the compounds or their salts. The compounds and their non-toxic salts exhibit valuable pharmacological properties as estrogenic, anti-estrogenic, progestanic and anti-tumour activity. Certain compounds of the group are useful as chemical intermediates for the preparation of pharmaceutically active compounds of the invention.
AU89702/82A 1981-10-26 1982-10-22 Alkane and alkene derivatives Ceased AU555477B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8132240 1981-10-26
GB08132240A GB2108486B (en) 1981-10-26 1981-10-26 Alkane and alkene derivatives and their preparation and use

Publications (2)

Publication Number Publication Date
AU8970282A AU8970282A (en) 1983-05-12
AU555477B2 true AU555477B2 (en) 1986-09-25

Family

ID=10525401

Family Applications (1)

Application Number Title Priority Date Filing Date
AU89702/82A Ceased AU555477B2 (en) 1981-10-26 1982-10-22 Alkane and alkene derivatives

Country Status (18)

Country Link
US (1) US4556677A (en)
EP (1) EP0078158B1 (en)
JP (1) JPS5879934A (en)
AT (1) ATE22065T1 (en)
AU (1) AU555477B2 (en)
CA (1) CA1310974C (en)
DD (1) DD211548A1 (en)
DE (1) DE3273219D1 (en)
DK (1) DK472082A (en)
FI (1) FI77842C (en)
GB (1) GB2108486B (en)
HU (1) HU193268B (en)
IE (1) IE54586B1 (en)
IL (1) IL67049A (en)
NO (1) NO159079C (en)
NZ (1) NZ202269A (en)
SU (1) SU1329615A3 (en)
ZA (1) ZA827742B (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2108486B (en) * 1981-10-26 1986-01-29 Farmos Group Ltd Alkane and alkene derivatives and their preparation and use
US4775660A (en) * 1984-08-02 1988-10-04 Fernand Labrie Treatment of breast cancer by combination therapy
US4666885A (en) * 1985-02-08 1987-05-19 Fernand Labrie Combination therapy for treatment of female breast cancer
US4760053A (en) * 1984-08-02 1988-07-26 Fernand Labrie Combination therapy for selected sex steroid dependent cancers
US4895715A (en) * 1988-04-14 1990-01-23 Schering Corporation Method of treating gynecomastia
ES2077675T3 (en) * 1989-03-10 1995-12-01 Endorecherche Inc COMBINED THERAPY FOR THE TREATMENT OF ESTROGEN SENSITIVE DISEASES.
NL1018247C2 (en) 2001-06-08 2002-12-10 Sara Lee De Nv Device for preparing a beverage suitable for consumption such as coffee.
JP2004010479A (en) * 2002-06-03 2004-01-15 Japan Science & Technology Corp New solid pharmaceutical preparation comprising block copolymer and anthracycline anticancer agent, and method for producing the same
CN102317464B (en) * 2008-12-12 2014-10-29 塞莱西翁有限公司 Biological Synthesis of Difunctional Alkanes from Carbohydrate Feedstocks
FR3071837B1 (en) * 2017-09-29 2019-11-01 Institut National De La Recherche Agronomique CHEMICALLY STABLE LIGNIN DERIVATIVE AND PROCESS FOR PREPARING THE SAME

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1306604A (en) * 1959-03-03 1962-10-19 Ferrosan Ab Process for preparing substituted bisphenylethylenes
GB1289966A (en) * 1968-12-24 1972-09-20
US3661976A (en) * 1969-05-16 1972-05-09 Parke Davis & Co 4,4'-(2-cycloalkyl-alkylidene) diphenols and ethers and esters thereof
BE793686A (en) * 1972-01-07 1973-07-04 Beecham Group Ltd BIOLOGICALLY ACTIVE DI-ARYL COMPOUNDS
GB2108486B (en) * 1981-10-26 1986-01-29 Farmos Group Ltd Alkane and alkene derivatives and their preparation and use

Also Published As

Publication number Publication date
HU193268B (en) 1987-09-28
AU8970282A (en) 1983-05-12
CA1310974C (en) 1992-12-01
EP0078158A3 (en) 1984-01-18
NO159079B (en) 1988-08-22
FI77842B (en) 1989-01-31
DD211548A1 (en) 1984-07-18
DK472082A (en) 1983-04-27
IE54586B1 (en) 1989-12-06
EP0078158B1 (en) 1986-09-10
IE822551L (en) 1983-04-26
ATE22065T1 (en) 1986-09-15
NO823537L (en) 1983-04-27
IL67049A (en) 1987-07-31
FI823465L (en) 1983-04-27
JPH0239492B2 (en) 1990-09-05
ZA827742B (en) 1983-08-31
EP0078158A2 (en) 1983-05-04
GB2108486A (en) 1983-05-18
JPS5879934A (en) 1983-05-13
FI823465A0 (en) 1982-10-12
NZ202269A (en) 1985-05-31
SU1329615A3 (en) 1987-08-07
GB2108486B (en) 1986-01-29
DE3273219D1 (en) 1986-10-16
NO159079C (en) 1988-11-30
US4556677A (en) 1985-12-03
FI77842C (en) 1989-05-10

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